Top Remote Senior Level Sales Leadership Jobs in Boston, MA

Lead the North America services go-to-market as the sales-facing professional services leader. Drive services positioning and attach rates, manage escalations, ensure high-quality value delivery, oversee at‑risk renewals, and represent PS in QBRs. Coach and develop teams, partner with sales on complex deals, and translate systemic issues into actionable improvement plans tied to commercial outcomes.

Lead a field sales team to drive zone sales and aftersales performance across assigned dealerships. Build dealer relationships, coach district managers, execute market growth and retention strategies, oversee digital marketing and inventory performance, ensure dealer compliance and training, and administer contractual and operational standards. Requires frequent travel and strong automotive business acumen.

Lead and develop a national B2B sales organization: manage quota-carrying AEs, coach through complex deals, drive pipeline/forecasting discipline, enablement, cross-functional alignment, participate in customer meetings and negotiations, and scale sales processes and playbooks.

Lead and grow a Central-region mid-market sales organization targeting employers (50–9,999 lives). Manage Regional Directors and AEs, set and execute sales strategy, develop broker/partner relationships, hit revenue targets, collaborate cross-functionally, and ensure compliance. Coach and scale a high-performing team focused on measurable impact and adoption of AI-enabled tools.

Lead and coach a virtual network of independent, licensed Medicare insurance agents to drive revenue growth, monitor performance, ensure CMS compliance, collaborate with cross-functional teams, and improve sales processes and customer experience.

Lead and develop an enterprise sales team to acquire, grow, and retain health system customers. Build commercial strategy, coach sellers on account planning and negotiations, drive data-informed revenue growth, recruit and retain sales talent, and align cross-functional teams to scale repeatable processes and improve customer outcomes.

Lead and scale a team of Key & Enterprise Account Executives across US Travel, New Markets, and Canada. Drive GTM strategy, executive stakeholder management, complex deal negotiation, cross-functional deal orchestration, forecasting rigor, and post-close launch/expansion. Recruit, coach, and hold the team accountable while traveling regularly to accelerate deals and represent Affirm at industry events.

Lead a 70+ person inside sales organization, owning strategy and execution for new sales, renewals, and win-backs. Drive revenue targets, forecasting, analytics-driven process improvement, cross-functional campaigns, tooling/automation with Technology, and talent development to scale a high-volume, short-cycle fintech sales operation.

The Channel Leader drives Zerigo Health's channel strategy through partner relationships, facilitating sales, managing account health, and ensuring growth.

Lead and manage Regional Senior Sales Directors across the East to drive strategic sales, set goals and quotas, build forecasts and budgets, develop personnel, communicate corporate strategy, and ensure attainment of multimillion-dollar revenue targets while collaborating with cross-functional teams.